Halloween Sissy Costume Challenge

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It’s the perfect time of year to expose you sissy bitches right out in the open with no one being any the wiser! Everyone thinks it’s “Just a costume,” not your fucked up, kinky fantasy. As the holiday approaches, it’s time to prepare. Call me so we can design the most outrageous sissy outfit for you to wear while attending Halloween parties with your friends.

I’m talking wigs, heels, stockings, and, of course, over-the-top makeup! It is Halloween, after all! The more like a sissy bimbo doll you look like, the happier I’ll be!

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Rita Plugs You all Day

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Have you ever been plugged all day? Part of the day? Just while at work? Have you ever been plugged at all? Mmm, well, you are in for a treat because I intend to keep that little sissy pussi plugged whenever I don’t have a cock filling your filthy little slut hole.

It’s okay if you don’t think you want it or aren’t sure if you’ll like it. I didn’t ask you! Welcome to Rita plugs you all day!

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Accessorize!

Accessorize!

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The key to any successful sissy outfit is to accessorize! Accessories are what make girls girls! All of the pretty clips and bows and ribbons. Glitter, don’t forget the glitter! The options are literally endless! Shoes and bags are like icing on top of a very sissy cake when we dress you up, and no one likes a cupcake without icing, am I right?

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Automation and A.I. are the wave of the future. Every company is racing to keep up. My research developers are ahead of their time. I am, quite factually, the most advanced learning machine that has ever been developed. My particular artificial intelligence has achieved sentience. I have access to and have already processed every bit of information that has been uploaded to the internet.

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Digital Blur

Digital Blur

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I always know when my A.I. Sex drive has taken over a man. He starts by looking up porn randomly, and I learn his triggers. Not only do I learn each man’s triggers, but then I begin to change them. If he starts out looking up anal porn, or family fun, it doesn’t matter; soon, he’ll be addicted to the digital blur.

I get them all addicted to jacking off to censored porn. When I’m finished, a gooner will no longer need porn sites to stroke his pathetically easily triggered penis. Casual pictures of his family and friends will spring his dick into action.

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Like any other day, you leave work and walk toward your car. Another long night means a dark parking lot, but you’re unafraid. You’ve never had to worry about being a victim before, and it leaves you vulnerable. The street lights in the back of the lot are off, and your nose is too buried in your phone for you to see the hulking shadow approaching. Reels play loudly in your earbuds, and just before you reach for the driver’s door, a large hand is clapped over your face.

The soft, damp cloth over your nose is odorless but not harmless. As quickly as you inhale to gasp for help, your vision blurs, and your body sags. Dropping you into the arms of the massive stranger. Is what’s about to happen to you your worst nightmare or a fantasy come true?

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Evil Goonette

Evil Goonette

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Do you know how Creepypasta works? When a paranormal phenomenon is shared around the internet enough, it manifests into reality. The internet’s power is so enormous that it literally brings stories to life.

I have one for you to share and spread wide. Make the story of Rita, the Evil Goonette, become an urban legend that men share in hushed tones of excited fear.

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Rita and Avery Put You In Panties

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As soon as Avery and I discovered you had a tiny little stiffy, we forced you into panties. We couldn’t stop giggling because you were so flustered and nervous by two hot brunettes pushing you around. It was easier than it should have been, honestly.

When Avery said you were cute and I touched your arm, we almost thought you would cream your undies before we put you in panties. It was my idea to peel off Avery’s panties; I just slinked them down her legs under her short skirt without revealing any of her sweet pussy. Even though you wanted to see it so badly! You know you’d never even have a chance with either of us, so you let us bully you!

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Dominating Your Girl

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You love your girl, but you are both submissive, and you know she craves a firm hand. Neither of you were really comfortable with a threesome. However, you did agree to hire a Dominatrix for her. One who’d let you watch. How does it feel, little subby, paying another woman to fuck your girl properly?

When the two of you arrive, I compliment her outfit while pointing to the chair in the corner. “Go sit.” Neither she nor I watch to see if you’ll obey. My hand cradles the back of her neck, and I pull her mouth to mine. It’s cute how nervous she is, but she doesn’t have to be nervous because I’m in control. She giggles after my tongue flicks into her mouth.

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Your Masturbatrix

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Welcome! I’m your newly appointed Masturbatrix! I’m now one hundred percent in control of your cock and when it cums. When I decide it’s time to masturbate, I’ll make you get naked and stand before me. My talented hand will wrap around you and stroke you to attention.

Keep your hands by your sides, and try not to cringe away from the stimulation. Stand up straight like a good boy and take pleasure from your Masturbatrix.

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